A triarylamine compound and an organic electroluminescent device thereof

Abstract

The present invention provides a triarylamine compound and an organic electroluminescent device thereof, specifically relating to the technical field of organic electroluminescent materials. The triarylamine compound has a high hole mobility, a high glass transition temperature, and good thermal stability. It can effectively improve the injection and transport efficiency of holes, reduce the hole injection barrier, and increase the recombination probability of excitons within the light-emitting layer. When applied to the hole transport region of an organic electroluminescent device, it can effectively reduce the device's driving voltage and improve the device's luminous efficiency and service life. Furthermore, the triarylamine compound also has a high refractive index. When applied to the cover layer of an organic electroluminescent device, it can effectively couple light trapped within the device out, reducing total internal reflection and waveguide loss of light within the device, enhancing the device's light extraction efficiency, and thereby improving the device's luminous efficiency and service life.

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a triarylamine compound and an organic electroluminescent device thereof. Background Art

[0002] Organic Light-Emitting Diode (OLED) is one of the most promising new display technologies. It has the advantages of light weight, small thickness, wide viewing angle, fast response speed, low energy consumption, high efficiency, wide adaptability, and good color purity. It is widely used in many fields such as lighting and display, and has broad application prospects.

[0003] OLED includes a cathode, an anode, and an organic layer. The organic layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, a covering layer, etc. These organic functional layers play an important role in improving the driving voltage, luminous efficiency, color purity, service life and other performance of OLED devices. The luminescence principle of OLED is that holes and electrons are injected from the anode and cathode into the organic layer respectively under the action of an external electric field, and then enter the light-emitting layer through the hole transport region and the electron transport region respectively. The two recombine in the light-emitting layer to generate excitons and release energy. The excitons migrate under the action of the electric field and transfer energy to the light-emitting substance in the light-emitting layer. The electrons in the molecules of the light-emitting substance jump from the ground state to the excited state, and then from the excited state back to the ground state. In this process, energy is released in the form of light.

[0004] Hole transport materials are a crucial component of organic electroluminescent devices. Their function is to effectively transfer holes, improve hole injection and transport efficiency, lower the hole injection barrier, and trap electrons within the light-emitting layer, thereby maximizing carrier recombination. High-quality hole transport materials should possess excellent properties such as high hole mobility, good thermal stability, excellent film-forming properties, and an appropriate HOMO energy level. However, most currently used hole transport materials suffer from poor film-forming and thermal stability, as well as low hole mobility. These issues can affect the luminous efficiency and lifespan of devices.

[0005] Therefore, in order to better solve the problems of low luminous efficiency and service life of organic light-emitting devices, the research focus of hole transport materials is to improve the hole mobility, thermal stability and film-forming properties of the materials, thereby improving the luminous efficiency of the devices and extending the service life of the devices. Summary of the Invention

[0006] To address the above technical issues, the present invention provides a triarylamine compound and an organic electroluminescent device thereof. When applied to the hole transport region or cover layer of an organic electroluminescent device, the triarylamine compound can effectively improve the luminous efficiency of the organic electroluminescent device and extend the service life of the organic electroluminescent device. The technical solution of the present invention is as follows:

[0007] The present invention provides a triarylamine compound, wherein the triarylamine compound is represented by the structure shown in Formula 1:

[0008]

[0009] The A is selected from Formula 2:

[0010]

[0011] R1 is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C3-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, a group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C8 aliphatic ring, and a substituted or unsubstituted 5-30 membered heteroaryl;

[0012] The R2 is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, and substituted or unsubstituted silyl;

[0013] The a is independently selected from 0, 1, 2, 3 or 4; when the a is greater than 1, two or more R2 are the same or different from each other, or two adjacent R2 can be connected to form a substituted or unsubstituted C6-C30 aromatic ring;

[0014] The L is selected from any one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrenyl group, and a substituted or unsubstituted trimphenylene group;

[0015] The Ar1 is selected from Formula 3-1 or Formula 3-2:

[0016]

[0017] The R3 is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, and substituted or unsubstituted C6-C30 aryl; two adjacent R3s may be connected to form a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, or a substituted or unsubstituted triphenylene ring; and at least one of the R3s is selected from a substituted or unsubstituted adamantyl group;

[0018] The R a 、R b Any one independently selected from hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C6-C30 aromatic ring fused with a substituted or unsubstituted C3-C8 aliphatic ring; or said R a 、R b They may be linked to form a substituted or unsubstituted spirofluorene ring or a substituted or unsubstituted aliphatic ring;

[0019] The b is independently selected from 1, 2, 3, 4 or 5; when the b is greater than 1, two or more R3 are the same or different from each other; the n is selected from 0, 1, 2 or 3;

[0020] The Ar2 is selected from Formula 4:

[0021]

[0022] The X1 is selected from any one of O, S or NR5; the X2 is selected from any one of a single bond, O, S or NR6;

[0023] The R4 is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, a group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C8 aliphatic ring, and a substituted or unsubstituted 5-30 membered heteroaryl;

[0024] The R5 and R6 are independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, a group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C8 aliphatic ring, and a substituted or unsubstituted 5-30 membered heteroaryl; or the R5 may be directly bonded to L2;

[0025] The c is independently selected from 0, 1, 2, 3 or 4; when the c is greater than 1, two or more R4s are the same or different from each other, or two adjacent R4s can be connected to form a substituted or unsubstituted C6-C30 aromatic ring;

[0026] The L1 and L2 are independently selected from any one of a single bond or a substituted or unsubstituted C6-C30 arylene group.

[0027] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains any one or a combination of at least two of the triarylamine compounds according to any one of claims 1 to 7.

[0028] Beneficial effects:

[0029] The present invention provides a triarylamine compound and an organic electroluminescent device thereof. The triarylamine compound has a high hole mobility, a high glass transition temperature, good thermal stability and an appropriate HOMO energy level, can improve the injection and transport efficiency of holes, reduce the hole injection barrier, prevent some electrons from passing through the light-emitting layer, increase the recombination probability of excitons in the light-emitting layer, and achieve the maximum load of carriers. When the triarylamine compound is applied to the hole transport region of the organic electroluminescent device, the luminous efficiency and service life of the device can be effectively improved, and the driving voltage of the device can be reduced. At the same time, the triarylamine compound also has a high refractive index. When applied to the cover layer of the organic electroluminescent device, the triarylamine compound can couple out light trapped in the device, reduce total reflection and waveguide loss of light inside the device, enhance the light extraction efficiency of the device, and thus improve the luminous efficiency of the organic electroluminescent device. DETAILED DESCRIPTION

[0030] The following will be a clear and complete description of the technical solutions of the specific embodiments of the present invention. Obviously, the embodiments described are only part of the embodiments of the present invention, not all of them. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without making any creative efforts shall fall within the scope of protection of the present invention.

[0031] In the compounds of the present invention, any atom not designated as a specific isotope is included as any stable isotope of that atom, and includes the atom at both its natural isotopic abundance and unnatural abundance.

[0032] The halogen atom mentioned in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0033] The alkyl group described in the present invention refers to a hydrocarbon group formed by missing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but is not limited thereto; the branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomeric groups of n-pentyl, isomeric groups of n-hexyl, isomeric groups of n-heptyl, isomeric groups of n-octyl, isomeric groups of n-nonyl, isomeric groups of n-decyl, etc., but is not limited thereto. The above-mentioned alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl.

[0034] The cycloalkyl group described herein refers to a hydrocarbon group formed by removing a hydrogen atom from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, and norbornane. Preferred cycloalkyl groups include cyclopentane, cyclohexane, 1-adamantane, 2-adamantane, and norbornane.

[0035] The "substituted or unsubstituted silyl group" in the present invention refers to -Si(R z )3 groups, wherein each R z The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkenyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C15 alicyclic ring fused with C6-C30 aromatic ring, substituted or unsubstituted C3-C15 alicyclic ring fused with C2-C30 heteroaromatic ring. Preferably, each R z The same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl. The number of carbon atoms in the alkyl group is preferably 1 to 20, preferably 1 to 15, more preferably 1 to 10, and most preferably 1 to 8. The number of carbon atoms in the cycloalkyl group is preferably 3 to 20, preferably 3 to 15, more preferably 3 to 10, and most preferably 3 to 7. Preferably, each R zThe same or different groups are selected from the following groups: hydrogen, deuterium, tritium, cyano, halogen, nitro, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, substituted or unsubstituted heptyl, substituted or unsubstituted octyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted adamantyl, substituted or unsubstituted norbornyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, etc., but are not limited thereto.

[0036] The aryl group described in the present invention refers to a monovalent group remaining after removing a hydrogen atom from the aromatic carbon nucleus of an aromatic compound molecule. It can be a monocyclic aryl group, a polycyclic aryl group, or a condensed aryl group, preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl group refers to an aryl group with only one aromatic ring in the molecule, such as, but not limited to, phenyl; the polycyclic aryl group refers to an aryl group containing two or more independent aromatic rings in the molecule, such as, but not limited to, biphenyl and terphenyl; the condensed aryl group refers to an aryl group containing two or more aromatic rings in the molecule and fused together by sharing two adjacent carbon atoms, such as, but not limited to, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluorenyl, benzofluorenyl, triphenylene, fluoranthenyl, spirobifluorenyl, etc. The above-mentioned aryl group is preferably phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl.

[0037] The heteroaryl group described in the present invention refers to a general term for a group in which one or more aromatic carbon atoms in the aromatic nucleus are replaced by a heteroatom, wherein the heteroatom includes but is not limited to oxygen, sulfur, nitrogen or phosphorus atoms, and preferably has 5 to 30 ring atoms (5 to 30 members), more preferably 6 to 24 ring atoms (6 to 24 members), particularly preferably 6 to 13 ring atoms (6 to 13 members), and most preferably 6 to 12 ring atoms (6 to 12 members); in addition, preferably has 1 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms; the attachment site of the heteroaryl group may be located on a ring-forming carbon atom or a ring-forming nitrogen atom, and the heteroaryl group may be a monocyclic heteroaryl group, a polycyclic heteroaryl group or a condensed-ring heteroaryl group. The monocyclic heteroaryl groups include, but are not limited to, pyridyl, pyrimidinyl, triazine, furyl, thienyl, pyrrolyl, imidazolyl, etc.; the polycyclic heteroaryl groups include, but are not limited to, bipyridyl, bipyrimidinyl, phenylpyridyl, etc.; the fused-ring heteroaryl groups include, but are not limited to, quinolyl, isoquinolyl, indolyl, benzothiophenyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, benzocarbazolyl, acridinyl, 9,10-dihydroacridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, etc., but are not limited to. The above-mentioned heteroaryl group is preferably pyridyl, pyrimidinyl, thienyl, furyl, benzothienyl, benzofuranyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenoxathiyl, spirofluorenyloxanthenyl, spirofluorenylthioanthenyl, etc.

[0038] The group formed by the fusion of an aromatic ring and an aliphatic ring according to the present invention refers to a general term for a monovalent group formed by fusion of an aromatic ring and an aliphatic ring (cycloalkyl, cycloalkenyl, cycloalkynyl) and removing one hydrogen atom. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The aliphatic ring preferably has 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, further preferably 3 to 12 carbon atoms, and most preferably 3 to 8 carbon atoms. Examples include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, benzocycloheptenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, butenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, butenyl, but not limited thereto.

[0039] The arylene group in the present invention means an aryl group having two bonding sites, that is, a divalent group. The description of the aryl group provided above can be applied thereto, except that the arylene group is a divalent group.

[0040] The heteroarylene group in the present invention means a heteroaryl group having two bonding sites, that is, a divalent group. The description of the aryl group provided above can be applied thereto, except that the heteroarylene group is a divalent group.

[0041] The term "unsubstituted" in the context of "substituted or unsubstituted" herein means that no hydrogen atom on the group is replaced by any substituent. The term "substituted" in the context of "substituted or unsubstituted" herein means that at least one hydrogen atom on the group is replaced by a substituent, and the position of substitution is not limited as long as the position is the position where the hydrogen atom is replaced. When multiple hydrogen atoms are replaced by multiple substituents, the multiple substituents may be the same or different.

[0042] The substituents in the "substituted or unsubstituted" of the present invention can be independently selected from deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkenyl, substituted or unsubstituted C1-C12 alkynyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C3-C12 cycloalkynyl, substituted or unsubstituted C6 ~C30 aryl, a group formed by condensation of a substituted or unsubstituted C6~C30 aromatic ring and a substituted or unsubstituted C3~C8 aliphatic ring, or a substituted or unsubstituted 5-30 membered heteroaryl; preferably one or more of deuterium, tritium, halogen, cyano, C1~C12 alkyl, C3~C12 cycloalkyl, C6~C30 aryl, 5-30 membered heteroaryl. When multiple substituents are present, multiple substituents may be present. The substituents may be the same or different from each other; specifically, they may be selected from the following groups: deuterium, fluorine, chlorine, bromine, iodine, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, bornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, perylene, pyrenyl, benzocyclobutane, benzocyclohexane, benzophenone ... One or more of pentyl, benzocyclohexyl, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, cyclohexadienyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirobifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, when there are multiple substituents, the multiple substituents are the same or different from each other.

[0043] In this specification, "*-" means a part connected to another substituent. "*-" can be connected to any optional position of the group / fragment to which it is connected. For example express And so on.

[0044] In this specification, when the position of a substituent on a ring is not fixed, it means that it can be attached to any of the corresponding optional positions of the ring. For example, Can represent Can represent Can represent And so on.

[0045] In this specification, when a substituent or a bond at a connection site runs through two or more rings, it indicates that it can be connected to any of the two or more rings, specifically any of the corresponding optional sites of the ring. For example, Can represent Can represent And so on.

[0046] The term "connected to form a ring" as used in the present invention means that the groups are connected to each other through chemical bonds, and optionally form double bonds / triple bonds, and may constitute aromatic groups, as shown in the following example:

[0047]

[0048] In the present invention, the ring formed by connection can be an aromatic ring system, an aliphatic ring system or a ring system formed by the fusion of the two, and can be a three-membered ring, a four-membered ring, a five-membered ring, a six-membered ring or a fused ring. Examples may include benzene, naphthalene, indene, fluorene, cyclopentene, cyclopentane, cyclohexene, cyclohexane, anthracene, phenanthrene, pyrene, pyridine, pyrimidine, etc., but are not limited thereto.

[0049] The present invention provides a triarylamine compound, wherein the triarylamine compound is represented by the structure shown in Formula 1:

[0050]

[0051] The A is selected from Formula 2:

[0052]

[0053] R1 is selected from any one of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C3-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, a group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C8 aliphatic ring, and a substituted or unsubstituted 5-30 membered heteroaryl;

[0054] The R2 is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, and substituted or unsubstituted silyl;

[0055] The a is independently selected from 0, 1, 2, 3 or 4; when the a is greater than 1, two or more R2 are the same or different from each other, or two adjacent R2 can be connected to form a substituted or unsubstituted C6-C30 aromatic ring;

[0056] The L is selected from any one of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted phenanthrenyl group, and a substituted or unsubstituted trimphenylene group;

[0057] The Ar1 is selected from Formula 3-1 or Formula 3-2:

[0058]

[0059] The R3 is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, and substituted or unsubstituted C6-C30 aryl; two adjacent R3s may be connected to form a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, or a substituted or unsubstituted triphenylene ring; and at least one of the R3s is selected from a substituted or unsubstituted adamantyl group;

[0060] The R a 、R b Any one independently selected from hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C6-C30 aromatic ring fused with a substituted or unsubstituted C3-C8 aliphatic ring; or said R a 、R b They may be linked to form a substituted or unsubstituted spirofluorene ring or a substituted or unsubstituted aliphatic ring;

[0061] The b is independently selected from 1, 2, 3, 4 or 5; when the b is greater than 1, two or more R3 are the same or different from each other; the n is selected from 0, 1, 2 or 3;

[0062] The Ar2 is selected from Formula 4:

[0063]

[0064] The X1 is selected from any one of O, S or NR5; the X2 is selected from any one of a single bond, O, S or NR6;

[0065] The R4 is independently selected from any one of hydrogen, deuterium, tritium, halogen, cyano, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, a group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C8 aliphatic ring, and a substituted or unsubstituted 5-30 membered heteroaryl;

[0066] The R5 and R6 are independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, a group formed by condensing a substituted or unsubstituted C6-C30 aromatic ring and a substituted or unsubstituted C3-C8 aliphatic ring, and a substituted or unsubstituted 5-30 membered heteroaryl; or the R5 may be directly bonded to L2;

[0067] The c is independently selected from 0, 1, 2, 3 or 4; when the c is greater than 1, two or more R4s are the same or different from each other, or two adjacent R4s can be connected to form a substituted or unsubstituted C6-C30 aromatic ring;

[0068] The L1 and L2 are independently selected from any one of a single bond or a substituted or unsubstituted C6-C30 arylene group.

[0069] Preferably, the substituent in the "substituted or unsubstituted" is selected from one or more of deuterium, halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C1-C12 alkenyl, substituted or unsubstituted C1-C12 alkynyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C12 cycloalkenyl, substituted or unsubstituted C3-C12 cycloalkynyl, substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted 5-30 membered heteroaryl. When multiple substituents are present, the multiple substituents are the same or different from each other.

[0070] Preferably, R1 is selected from hydrogen, deuterium, tritium, halogen, cyano, trifluoromethyl, substituted or unsubstituted any one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, benzocyclobutane, benzocyclopentane, benzocyclohexane alkyl, benzophenone, benzothiophene ...

[0071] Preferably, the "substituted or unsubstituted" substituent in R1 is selected from one or more of deuterium, tritium, halogen, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, and norbornane. When multiple substituents are present, the multiple substituents are the same or different from each other.

[0072] Preferably, the R2 is independently selected from hydrogen, deuterium, tritium, halogen, cyano, trifluoromethyl, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, or triphenylsilyl, or two adjacent R2 groups may be connected to form a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, or a substituted or unsubstituted phenanthrene ring;

[0073] Preferably, the "substituted or unsubstituted" substituents in R2 are independently selected from one or more of deuterium, tritium, halogen, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, and norbornane. When multiple substituents are present, the multiple substituents are the same or different from each other.

[0074] Preferably, Ar1 is selected from any one of the following groups:

[0075]

[0076] The R3 is independently selected from hydrogen, deuterium, tritium, halogen, cyano, trifluoromethyl, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, bornyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, fluorenyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, or triphenylsilyl; or two adjacent R3s may be linked to form a substituted or unsubstituted phenyl ring or a substituted or unsubstituted naphthalene ring; and at least one of the R3s is selected from a substituted or unsubstituted adamantyl group;

[0077] The R a 、R b independently selected from hydrogen, deuterium, tritium, halogen, cyano, trifluoromethyl, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, fluorenyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl;

[0078] The R c independently selected from hydrogen, deuterium, tritium, halogen, cyano, trifluoromethyl, substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl;

[0079] Said b1 is independently selected from 1, 2, 3, 4 or 5; said b2 is independently selected from 1, 2, 3 or 4; said b3 is independently selected from 1, 2, 3, 4, 5, 6 or 7; said b4 is independently selected from 1, 2, 3, 4, 5 or 6; said b5 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8 or 9; said b6 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8; said b7 is independently selected from 1, 2 , 3, 4, 5, 6, 7, 8, 9 or 10; b8 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; b9 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; when b1, b2, b3, b4, b5, b6, b7, b8 or b9 is greater than 1, two or more R3 are the same or different;

[0080] Preferably, the R3, R a 、R b 、R cThe substituents of "substituted or unsubstituted" are independently selected from one or more of deuterium, tritium, halogen, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornane, phenyl, biphenyl and naphthyl. When multiple substituents are present, the multiple substituents may be the same or different from each other.

[0081] Preferably, one, two, three, four or more of the R3 are selected from substituted or unsubstituted adamantyl groups;

[0082] More preferably, the substituents of the "substituted or unsubstituted adamantyl group" are independently selected from any one of deuterium, tritium, halogen, cyano, C1-C10 alkyl, C3-C12 cycloalkyl, and C6-C20 aryl;

[0083] More preferably, the substituents of the “substituted or unsubstituted adamantyl” are independently selected from deuterium, tritium, halogen, cyano, trifluoromethyl, or any one of the following groups substituted or unsubstituted by deuterium: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, bornyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, and triphenylsilyl.

[0084] Preferably, Ar2 is selected from any one of the following groups:

[0085]

[0086] R4 is independently selected from hydrogen, deuterium, tritium, halogen, cyano, trifluoromethyl, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, or triphenylsilyl;

[0087] Said R5 and R6 are independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, benzocyclobutane, benzocyclopentane, benzocyclohexane, fluorene, benzophenone ... 1,2-D,3-D,4-D,5-D,6-D,7-D,8-D,9-D,10-D,11-D,12-D,13-D,14-D,15-D,16-D,17-D,18-D,19-D,20-D,21-D,22-D,23-D,24-D,25-D,26-D,27-D,28-D,29-D,30-D,31-D,32-D,33-D,34-D,35-D,36-D,37-D,38-D,39-D,41-D,42-D,43-D,44-D,51-D,45-D,46-D,47-D,48-D,49-D,52-D,53-D,54-D,55-D,56-D,57-D,58-D,59-D,61-D,62-D,63-D,64-D,65-D,67-D,68-D,69-D,71-D,72-D,73-D,74-D,75-D,76-D,77-D,71-D,73-D,74-D,75-D,72-D,73-D,74-D,75 ...3-D,7

[0088] Said c1 is independently selected from 0, 1, 2, 3 or 4; said c2 is independently selected from 0, 1, 2, 3, 4, 5 or 6; said c3 is independently selected from 0, 1, 2, 3, 4, 5, 6, 7 or 8; when said c1, c2 or c3 is greater than 1, two or more R4 are the same or different from each other;

[0089] Preferably, the "substituted or unsubstituted" substituents in R4, R5, and R6 are independently selected from one or more of deuterium, tritium, halogen, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, and naphthyl. When multiple substituents are present, the multiple substituents are the same or different from each other.

[0090] Preferably, L is selected from a single bond or any one of the following groups:

[0091]

[0092] R7 is independently selected from hydrogen, deuterium, tritium, halogen, cyano, trifluoromethyl, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, or triphenylsilyl;

[0093] The e1 is independently selected from 0, 1, 2, 3 or 4; the e2 is independently selected from 0, 1, 2 or 3; the e3 is independently selected from 0, 1 or 2; when the e1, e2 or e3 is greater than 1, two or more R7 are the same or different, or two adjacent R7s may be connected to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring;

[0094] Preferably, the "substituted or unsubstituted" substituents in R7 are independently selected from one or more of deuterium, tritium, halogen, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, and naphthyl. When multiple substituents are present, the multiple substituents are the same or different from each other.

[0095] More preferably, L is selected from a single bond or any one of the following substituted or unsubstituted groups:

[0096]

[0097] The "substituted" group is selected from one or more of deuterium, tritium, halogen, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, and naphthyl. When multiple substituents are present, the multiple substituents are the same or different from each other.

[0098] Preferably, L1 and L2 are independently selected from a single bond or any one of the following groups:

[0099]

[0100] R8 and R9 are independently selected from hydrogen, deuterium, tritium, halogen, cyano, trifluoromethyl, or any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylene, fluorenyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, or triphenylsilyl; or two adjacent R8s may be linked to form a substituted or unsubstituted ring;

[0101] The f1 is independently selected from 0, 1, 2, 3 or 4; the f2 is independently selected from 0, 1, 2 or 3; the f3 is independently selected from 0, 1 or 2; when the f1, f2 or f3 is greater than 1, two or more R9 are the same or different from each other, or two adjacent R9 can be connected to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring;

[0102] Preferably, the "substituted or unsubstituted" substituents in R8 and R9 are independently selected from one or more of deuterium, tritium, halogen, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornane, phenyl, biphenyl, and naphthyl. When multiple substituents are present, the multiple substituents are the same or different from each other.

[0103] More preferably, L1 and L2 are independently selected from a single bond or any one of the following substituted or unsubstituted groups:

[0104]

[0105]

[0106] The "substituted" group is selected from one or more of deuterium, tritium, halogen, cyano, trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, adamantyl, norbornane, phenyl, biphenyl, and naphthyl. When multiple substituents are present, the multiple substituents are the same or different from each other.

[0107] Preferably, the triarylamine compound is selected from any one of the following structures:

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122] The above lists only some specific structural forms of the triarylamine compounds shown in Formula 1, but the present invention is not limited to these chemical structures listed. All structures based on Formula 1 and with substituents as defined above should be included.

[0123] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains any one or a combination of at least two of the triarylamine compounds described in the present invention.

[0124] The organic layer described in the present invention includes a hole transport region, a light-emitting layer, an electron transport region and a covering layer. The hole transport region includes functional layers such as a hole injection layer, a hole transport layer, an electron blocking layer, and a light-emitting auxiliary layer. The electron transport region includes functional layers such as a hole blocking layer, an electron transport layer, and an electron injection layer. The organic functional layers can be increased or decreased accordingly according to actual needs.

[0125] The organic layer described in the present invention may have a single-layer structure or a multi-layer structure. A single-layer structure includes a single layer containing a single material or a single layer containing multiple materials; a multi-layer structure includes multiple layers containing multiple materials. Specifically, the hole transport layer may include a first hole transport layer and a second hole transport layer, and the electron transport layer may include a first electron transport layer and a second electron transport layer. Specifically, the materials used for each organic functional layer may be selected from inorganic materials, organic materials, or inorganic-organic materials formed by a mixture of the two, but are not limited thereto.

[0126] Preferably, the organic layer is located between the anode and the cathode, and the organic layer comprises a hole transport region, wherein the hole transport region comprises any one or a combination of at least two of the triarylamine compounds described in the present invention.

[0127] Preferably, the hole transport region comprises a hole transport layer, and the hole transport layer comprises any one or a combination of at least two of the triarylamine compounds described in the present invention.

[0128] Preferably, the hole transport layer comprises a first hole transport layer and a second hole transport layer, and the second hole transport layer comprises any one or a combination of at least two of the triarylamine compounds described in the present invention.

[0129] Preferably, the organic layer is located outside one or more electrodes of the anode and the cathode, and the organic layer includes a covering layer, and the covering layer includes any one or a combination of at least two of the triarylamine compounds described in the present invention.

[0130] As the anode material of the present invention, a material with a high work function is preferably used. The anode can be a transmissive electrode, a reflective electrode, or a semi-transmissive electrode. When the anode is a transmissive electrode, the material used to form the anode can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof; when the anode is a semi-transmissive electrode or a reflective electrode, the material used to form the anode can be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode can have a single-layer structure or a multilayer structure including two or more layers. For example, the anode can have a single-layer structure of Al or a three-layer structure of ITO / Ag / ITO, but the structure of the anode is not limited thereto.

[0131] The hole injection layer material of the present invention preferably has a good hole-accepting ability and can be selected from any one or more of the following structures: metalloporphyrins, oligothiophenes, arylamine derivatives, perylene derivatives, hexanitrile hexaazatriphenylene compounds, quinacridone compounds, anthraquinone compounds, and polyaniline-based and polythiophene-based conductive polymers, but is not limited thereto.

[0132] As the hole transport layer material described in the present invention, a material with high hole mobility is preferred. In addition to the triarylamine compounds described in the present invention, any one or more of the following structures can also be selected: carbazole derivatives, triarylamine derivatives, benzyldiamine derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, hexanitrile hexaazatriphenylene compounds, quinacridone compounds, anthraquinone compounds, polyaniline, polythiophene, polyvinylcarbazole, etc., but not limited thereto. Preferably, the hole transport layer material uses the triarylamine compound described in the present invention.

[0133] The light-emitting layer material of the present invention may contain only a guest material, or may be in the form of a guest material dispersed in a host material, and may use two host materials to form a dual host material. The host material of the light-emitting layer not only needs to have bipolar charge transport properties, but also needs to have an appropriate energy level to effectively transfer the excitation energy to the guest light-emitting material. Examples of such materials include distyryl aryl derivatives, stilbene derivatives, carbazole derivatives, triarylamine derivatives, anthracene derivatives, and pyrene derivatives. The guest material may be selected from any one or more of the following structures: metal complexes (such as iridium complexes, platinum complexes, osmium complexes, rhodium complexes, etc.), anthracene derivatives, pyrene derivatives, perylene derivatives, etc., but is not limited thereto.

[0134] As the electron injection layer material of the present invention, a material with good electron injection and transmission capabilities is preferably selected. Any one or more of the following structures can be selected: alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, and other substances with high electron injection properties. Examples include Li, Ca, Sr, LiF, CsF, CaF2, BaO, Li2CO3, CaCO3, Li2C2O4, Cs2C2O4, CsAlF4, LiOx, Yb, Tb, etc., but are not limited thereto.

[0135] As the electron transport layer material of the present invention, a material having high electron mobility is preferred and can be selected from any one or more of the following structures: metal chelates, oxazoline derivatives, thiazole derivatives, diazole derivatives, azabenzene derivatives, diazaanthracene derivatives, silicon-containing heterocyclic compounds, boron-containing heterocyclic compounds, cyano compounds, quinoline derivatives, phenanthroline derivatives, benzimidazole derivatives, etc., but is not limited thereto.

[0136] As the hole blocking layer material of the present invention, a material with excellent hole blocking ability is preferred. The material used is required to have a T1 energy level higher than that of the light-emitting layer, so as to block the energy loss of the light-emitting layer. In addition, the HOMO energy level of the selected material should be lower than the HOMO energy level of the main material of the light-emitting layer, so as to play a role in blocking holes. Furthermore, the electron mobility of the hole blocking layer material used is 10 -6 cm 2 / Vs or more, which is beneficial to the transmission of electrons. Preferred are triazine derivatives, azabenzene derivatives, and the like.

[0137] As the cathode material of the present invention, a material with a low work function is preferred. The cathode can be selected from a transmissive electrode, a semi-reflective electrode, or a reflective electrode. When the cathode is a transmissive electrode, the material used to form the cathode can be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflective electrode, the material used to form the cathode can be selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds thereof, or mixtures thereof (e.g., a mixture of Ag and Mg), but is not limited thereto.

[0138] The cover layer material described herein is preferably a material with high light extraction efficiency. In addition to the triarylamine compounds described herein, any one or more of the following structures may be selected: for example, metal halides, oxides, nitrides, nitrogen oxides, sulfides, selenides, aromatic hydrocarbon compounds, heteroaromatic hydrocarbon compounds, aromatic amine compounds, and the like, but are not limited thereto. Preferably, the cover layer material is the triarylamine compound described herein.

[0139] The cathode, anode, organic layer, and cover layer can be formed by any of vacuum deposition, inkjet printing, sputtering, plasma deposition, ion plating, spin coating, dipping, and screen printing. The thickness of each layer is not particularly limited, provided that good device performance is achieved. Preferably, the organic layers are formed by vacuum deposition, inkjet printing, or spin coating.

[0140] The thickness of each organic layer and the cover layer is usually 5 nm to 100 μm, preferably 10 nm to 200 nm. The thickness of the anode and cathode is adjusted according to the required transparency.

[0141] The organic electroluminescent device of the present invention is mainly used in the fields of lighting and display, and can be specifically listed as smartphone display screens, tablet computer display screens, smart wearable device display screens, large-size displays such as televisions, digital cameras, VR and car taillights.

[0142] The present invention also provides a method for preparing the compound represented by Formula 1, but the preparation method of the present invention is not limited thereto. The following is merely an example of a synthetic route. The following synthetic routes all employ reaction types commonly used in organic synthesis. The reaction conditions (e.g., the selection of the types, amounts, and order and method of addition of reaction solvents, catalysts, ligands, bases, etc.) are not particularly limited and can be performed using conventional methods and operations.

[0143] The synthetic route of the compound shown in Formula 1:

[0144]

[0145] The Xa and Xb are independently selected from any one of Cl, Br and I.

[0146] The present invention is explained in more detail by the following examples, and the technical solutions and effects of the present invention are further illustrated, but it is not intended to limit the present invention. Based on this description, those skilled in the art will be able to implement the present invention and prepare other compounds and devices according to the present invention within the entire disclosed scope without inventive work.

[0147] Description of raw materials, reagents and characterization equipment:

[0148] The present invention has no particular limitation on the sources of the raw materials used in the following examples; commercially available raw materials or those well known to those skilled in the art can be used.

[0149] Mass spectrometry was performed using a British Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent;

[0150] The elemental analysis was performed using a Vario EL cube organic element analyzer from Elementar, Germany, with a sample mass of 5 to 10 mg.

[0151] Synthesis Example 1: Synthesis of Intermediate A-37

[0152]

[0153] Under nitrogen, a-37 (19.85 g, 80.00 mmol), b-37 (16.96 g, 80.00 mmol), K2CO3 (13.82 g, 100.00 mmol), and Pd(PPh3)4 (1.11 g, 0.96 mmol) were added to a reaction flask. 400 mL of a 2:1:1 toluene / ethanol / water mixture was added, stirred, and heated to reflux for 3 h. After the reaction, the reaction mixture was cooled to room temperature, toluene was added, and the phases were separated. The toluene phase was washed three times with distilled water, dried over anhydrous magnesium sulfate, and concentrated by rotary evaporation. The resulting solid was crystallized by cooling and filtered, and recrystallized from toluene to obtain intermediate A-37 (22.27 g, 83% yield); HPLC purity ≥99.69%. Mass spectrum: m / z: 335.1323 (theoretical value: 335.1310).

[0154] According to the above synthesis method, other intermediates A required for the present invention were synthesized. The relevant raw materials are shown in Table 101:

[0155] Table 101:

[0156]

[0157] Synthesis Example 2: Synthesis of Intermediate D-1

[0158]

[0159] Under nitrogen, c-1 (51.81 g, 120.00 mmol), d-1 (18.27 g, 120.00 mmol), and dichloromethane (150 mL) were added to a round-bottom flask. The temperature was lowered to 0-5°C, and trifluoromethanesulfonic acid (27.01 g, 180.00 mmol) was added dropwise. The mixture was stirred at this constant temperature for 3 h. After the reaction, aqueous sodium hydroxide solution was added to neutralize the mixture, and the mixture was extracted with dichloromethane. The mixture was allowed to stand for separation, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The resulting solid was then recrystallized from toluene to obtain intermediate D-1 (30.98 g, 53% yield); HPLC purity ≥99.76%. Mass spectrum: m / z 486.2125 (theoretical value: 486.2114).

[0160] According to the above synthesis method, other intermediates B required for the present invention were synthesized. The relevant raw materials are shown in Table 102:

[0161] Table 102:

[0162]

[0163]

[0164] Synthesis Example 3: Synthesis of Intermediate B-11

[0165]

[0166] Under nitrogen, c-1 (51.81 g, 120.00 mmol), d-1 (36.54 g, 240.00 mmol), and dichloromethane (300 mL) were added to a round-bottom flask. The temperature was lowered to 0-5°C, and trifluoromethanesulfonic acid (54.03 g, 360.00 mmol) was added dropwise. The mixture was stirred at this constant temperature for 3 h. After the reaction, aqueous sodium hydroxide solution was added to neutralize the reaction mixture, and the mixture was extracted with dichloromethane. The mixture was allowed to stand for separation, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The resulting solid was then recrystallized from toluene to obtain intermediate B-11 (23.32 g, 51% yield); HPLC purity ≥99.62%. Mass spectrum: m / z: 380.2258 (theoretical value: 380.2271).

[0167] Synthesis Example 4: Synthesis of Intermediate D-17

[0168]

[0169] Under nitrogen, e-17 (12.82 g, 55.00 mmol) and 50 mL of tetrahydrofuran were added to a reaction flask. The mixture was cooled to -78°C, and 8.15 mL of a 3.38 M solution of n-butyllithium in n-hexane was added. After stirring for 50 minutes, 35.63 mL of a tetrahydrofuran solution containing f-17 (15.34 g, 50.00 mmol) was added dropwise. Stirring was continued at -78°C for 50 minutes, then warmed to room temperature and stirred for 3 hours. The organic layer was extracted with saturated ammonium chloride solution, and the solvent was evaporated. The resulting residue was transferred to a reaction flask, 5 mL of hydrochloric acid was added, and the mixture was stirred at 100°C for 3 hours. The reaction solution was then poured into 50 mL of ice water, resulting in the precipitation of a solid. The crude solid was filtered and recrystallized from toluene to obtain intermediate D-17 (17.05 g, 77% yield); HPLC purity ≥99.57%. Mass spectrum m / z: 442.1132 (theoretical value: 442.1124).

[0170] Synthesis Example 5: Synthesis of Compound 1

[0171]

[0172] Synthetic intermediate C-1:

[0173] Under nitrogen, A-1 (9.16 g, 50.00 mmol), B-1 (14.56 g, 50.00 mmol), Pd(OAc)2 (0.13 g, 0.60 mmol), P(t-Bu)3 (0.12 g, 0.60 mmol), sodium tert-butoxide (8.17 g, 85.00 mmol), and 300 ml of toluene were added to a reaction flask. The mixture was stirred and heated under reflux for 5 h. After completion of the reaction, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The mixture was allowed to stand and separated, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Finally, it was recrystallized from toluene / methanol (10:3) to obtain intermediate C-1 (15.54 g, 79% yield) with HPLC purity ≥99.83%. Mass spectrum: m / z: 393.2084 (theoretical value: 393.2093).

[0174] Synthesis of compound 1:

[0175] Under nitrogen, C-1 (11.81 g, 30.00 mmol), D-1 (14.61 g, 30.00 mmol), Pd2(dba)3 (0.37 g, 0.40 mmol), BINAP (0.50 g, 0.80 mmol), sodium tert-butoxide (4.81 g, 50 mmol), and 150 ml of toluene were added to a reaction flask. The mixture was stirred and heated under reflux for 7 h. After completion of the reaction, the mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The mixture was allowed to stand for separation, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. Finally, it was recrystallized from toluene / methanol (10:1) to obtain compound 1 (18.49 g, 73% yield) with HPLC purity ≥99.92%. Mass spectrum m / z: 843.4453 (theoretical value: 843.4440). Theoretical element content (%): C 63 H 57 NO: C, 89.64; H, 6.81; N, 1.66. Measured element content (%): C, 89.60; H, 6.79; N, 1.69.

[0176] Synthesis Example 6: Synthesis of Compound 11

[0177]

[0178] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-11, B-11, and D-11 to obtain compound 11 (18.74 g, 74% yield). HPLC purity was ≥99.93%. Mass spectrum m / z: 843.4426 (theoretical value: 843.4440). Theoretical element content (%) C 63 H 57 NO: C, 89.64; H, 6.81; N, 1.66. Measured element content (%): C, 89.67; H, 6.78; N, 1.70.

[0179] Synthesis Example 7: Synthesis of Compound 17

[0180]

[0181] According to the preparation method of Synthesis Example 5, B-1 and D-1 were replaced with equimolar amounts of B-17 and D-17 to obtain compound 17 (17.04 g, 71% yield). HPLC purity was ≥99.96%. Mass spectrum m / z: 799.3458 (theoretical value: 799.3450). Theoretical element content (%) C 59 H 45NO2: C, 88.58; H, 5.67; N, 1.75. Measured element content (%): C, 88.61; H, 5.63; N, 1.77.

[0182] Synthesis Example 8: Synthesis of Compound 20

[0183]

[0184] According to the preparation method of Synthesis Example 5, B-1 and D-1 were replaced with equimolar amounts of B-20 and D-11 to obtain compound 20 (16.06 g, 75% yield). HPLC purity was ≥99.96%. Mass spectrum m / z: 713.3585 (theoretical value: 713.3596). Theoretical element content (%) C 53 H 39 D4NO: C, 89.16; H, 6.63; N, 1.96. Measured element content (%): C, 89.19; H, 6.59; N, 1.99.

[0185] Synthesis Example 9: Synthesis of Compound 21

[0186]

[0187] According to the preparation method of Synthesis Example 5, D-1 was replaced with an equal molar amount of D-11 to obtain compound 21 (16.19 g, yield 76%) with HPLC purity ≥ 99.98%. Mass spectrum m / z: 709.3357 (theoretical value: 709.3345). Theoretical element content (%) C 53 H 43 NO: C, 89.67; H, 6.11; N, 1.97. Measured element content (%): C, 89.70; H, 6.07; N, 1.92.

[0188] Synthesis Example 10: Synthesis of Compound 37

[0189]

[0190] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-37, B-17, and D-37 to obtain compound 37 (17.85 g, 69% yield). HPLC purity was ≥99.95%. Mass spectrum m / z: 861.3960 (theoretical value: 861.3971). Theoretical element content (%): C 65 H 51 NO: C, 90.56; H, 5.96; N, 1.62. Measured element content (%): C, 90.60; H, 5.91; N, 1.59.

[0191] Synthesis Example 11: Synthesis of Compound 54

[0192]

[0193] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-54, B-54, and D-54 to obtain compound 54 (16.74 g, 75% yield). HPLC purity was ≥99.97%. Mass spectrum m / z: 743.3037 (theoretical value: 743.3022). Theoretical element content (%): C 53 H 42 FNS: C, 85.56; H, 5.69; N, 1.88. Measured element content (%): C, 85.51; H, 5.72; N, 1.90.

[0194] Synthesis Example 12: Synthesis of Compound 61

[0195]

[0196] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-61, B-61, and D-61 to obtain compound 61 (17.73 g) with HPLC purity ≥99.94%. Mass spectrum m / z: 831.3889 (theoretical value: 831.3899). Theoretical element content (%) C 61 H 53 NS: C, 88.04; H, 6.42; N, 1.68. Measured element content (%): C, 88.09; H, 6.39; N, 1.70.

[0197] Synthesis Example 13: Synthesis of Compound 73

[0198]

[0199] According to the preparation method of Synthesis Example 5, A-1 and D-1 were replaced with equal moles of A-73 and D-73 to obtain compound 73 (17.65 g) with HPLC purity ≥99.94%. Mass spectrum m / z: 805.3692 (theoretical value: 805.3680). Theoretical element content (%) C 59 H 43 NS: C, 87.91; H, 6.38; N, 1.74. Measured element content (%): C, 87.88; H, 6.42; N, 1.76.

[0200] Synthesis Example 14: Synthesis of Compound 87

[0201]

[0202] According to the preparation method of Synthesis Example 5, A-1 and D-1 were replaced with equal moles of A-87 and D-11 to obtain compound 87 (18.94 g) with HPLC purity ≥99.91%. Mass spectrum m / z: 927.3882 (theoretical value: 927.3899). Theoretical element content (%) C 69 H 53 NS: C, 89.28; H, 5.76; N, 1.51. Measured element content (%): C, 89.31; H, 5.72; N, 1.48.

[0203] Synthesis Example 14: Synthesis of Compound 95

[0204]

[0205] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-95, B-95, and D-11 to obtain compound 95 (18.72 g) with HPLC purity ≥99.95%. Mass spectrum m / z: 890.4614 (theoretical value: 890.4600). Theoretical element content (%) C 67 H 58 N2: C, 90.30; H, 6.56; N, 3.14. Measured element content (%): C, 90.26; H, 6.59; N, 3.17.

[0206] Synthesis Example 16: Synthesis of Compound 106

[0207]

[0208] According to the preparation method of Synthesis Example 5, A-1 and D-1 were replaced with equal moles of A-106 and D-11 to obtain compound 106 (18.34 g) with HPLC purity ≥99.96%. Mass spectrum m / z: 860.4116 (theoretical value: 860.4130). Theoretical element content (%) C 65 H 52 N2: C, 90.66; H, 6.09; N, 3.25. Measured element content (%): C, 90.62; H, 6.12; N, 3.29.

[0209] Synthesis Example 17: Synthesis of Compound 121

[0210]

[0211] According to the preparation method of Synthesis Example 5, B-1 and D-1 were replaced with equal moles of B-121 and D-11 to obtain compound 121 (17.69 g) with HPLC purity ≥99.92%. Mass spectrum m / z: 785.3643 (theoretical value: 785.3658). Theoretical element content (%) C 59 H 47 NO: C, 90.16; H, 6.03; N, 1.78. Measured element content (%): C, 90.14; H, 6.07; N, 1.81.

[0212] Synthesis Example 18: Synthesis of Compound 127

[0213]

[0214] According to the preparation method of Synthesis Example 5, B-1 and D-1 were replaced with equimolar amounts of B-127 and D-127 to obtain compound 127 (17.30 g) with HPLC purity ≥99.95%. Mass spectrum m / z: 789.3921 (theoretical value: 789.3909). Theoretical element content (%) C 59 H 43 D4NO: C, 89.70; H, 6.51; N, 1.77. Measured element content (%): C, 89.65; H, 6.49; N, 1.80.

[0215] Synthesis Example 19: Synthesis of Compound 133

[0216]

[0217] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-133, B-121, and D-54 to obtain compound 133 (18.10 g) with HPLC purity ≥99.91%. Mass spectrum m / z: 861.3984 (theoretical value: 861.3971). Theoretical element content (%) C 65 H 51 NO: C, 90.56; H, 5.96; N, 1.62. Measured element content (%): C, 90.60; H, 5.93; N, 1.60.

[0218] Synthesis Example 20: Synthesis of Compound 147

[0219]

[0220] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-11, B-147, and D-147 to obtain compound 147 (17.54 g) with HPLC purity ≥99.94%. Mass spectrum m / z: 789.3918 (theoretical value: 789.3909). Theoretical element content (%) C 59 H 43 D4NO: C, 89.70; H, 6.51; N, 1.77. Measured element content (%): C, 89.68; H, 6.49; N, 1.82.

[0221] Synthesis Example 21: Synthesis of Compound 161

[0222]

[0223] According to the preparation method of Synthesis Example 5, C-1 and D-1 were replaced with equal moles of C-121 and D-161 to obtain compound 161 (18.88 g) with HPLC purity ≥99.97%. Mass spectrum m / z: 861.3961 (theoretical value: 861.3971). Theoretical element content (%) C 65 H 51 NO: C, 90.56; H, 5.96; N, 1.62. Measured element content (%): C, 90.60; H, 5.93; N, 1.57.

[0224] Synthesis Example 22: Synthesis of Compound 176

[0225]

[0226] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-176, B-121, and D-11 to obtain compound 176 (18.81 g) with HPLC purity ≥99.93%. Mass spectrum m / z: 835.3828 (theoretical value: 835.3814). Theoretical element content (%) C 63 H 49 NO: C, 90.50; H, 5.91; N, 1.68. Measured element content (%): C, 90.47; H, 5.87; N, 1.70.

[0227] Synthesis Example 23: Synthesis of Compound 178

[0228]

[0229] According to the preparation method of Synthesis Example 5, B-1 and D-1 were replaced with equimolar amounts of B-178 and D-178 to obtain compound 178 (16.98 g) with HPLC purity ≥ 99.94%. Mass spectrum m / z: 785.3641 (theoretical value: 785.3658). Theoretical element content (%) C 59 H 47 NO: C, 90.16; H, 6.03; N, 1.78. Measured element content (%): C, 90.19; H, 6.01; N, 1.82.

[0230] Synthesis Example 24: Synthesis of Compound 191

[0231]

[0232] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-191, B-121, and D-54 to obtain compound 191 (18.44 g) with HPLC purity ≥99.98%. Mass spectrum m / z: 877.3753 (theoretical value: 877.3742). Theoretical element content (%) C 65 H 51 NS: C, 88.90; H, 5.85; N, 1.59. Measured element content (%): C, 88.87; H, 5.87; N, 1.63.

[0233] Synthesis Example 25: Synthesis of Compound 201

[0234]

[0235] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-201, B-201, and D-11 to obtain Compound 201 (17.99 g) with HPLC purity ≥99.93%. Mass spectrum m / z: 894.4073 (theoretical value: 894.4087). Theoretical element content (%) C 66 H 50 D3NS: C, 88.55; H, 6.30; N, 1.56. Measured element content (%): C, 88.52; H, 6.26; N, 1.59.

[0236] Synthesis Example 26: Synthesis of Compound 204

[0237]

[0238] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-204, B-121, and D-204 to obtain Compound 204 (17.90 g) with HPLC purity ≥99.91%. Mass spectrum m / z: 851.3577 (theoretical value: 851.3586). Theoretical element content (%) C 63 H 49 NS: C, 88.80; H, 5.80; N, 1.64. Measured element content (%): C, 88.84; H, 5.78; N, 1.61.

[0239] Synthesis Example 27: Synthesis of Compound 216

[0240]

[0241] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-216, B-121, and D-11 to obtain compound 216 (18.94 g) with HPLC purity ≥99.94%. Mass spectrum m / z: 927.3882 (theoretical value: 927.3899). Theoretical element content (%) C 69 H 53 NS: C, 89.28; H, 5.76; N, 1.51. Measured element content (%): C, 89.30; H, 5.71; N, 1.48.

[0242] Synthesis Example 28: Synthesis of Compound 231

[0243]

[0244] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-231, B-231, and D-231 to obtain Compound 231 (18.60 g) with HPLC purity ≥99.96%. Mass spectrum m / z: 860.41115 (theoretical value: 860.4130). Theoretical element content (%) C 65 H 52 N2: C, 90.66; H, 6.09; N, 3.25. Measured element content (%): C, 90.68; H, 6.13; N, 3.22.

[0245] Synthesis Example 29: Synthesis of Compound 244

[0246]

[0247] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-244, B-244, and D-244 to obtain Compound 244 (18.94 g) with HPLC purity ≥99.92%. Mass spectrum m / z: 941.4728 (theoretical value: 941.4709). Theoretical element content (%) C 70 H 59 N3: C, 89.23; H, 6.31; N, 4.46. Measured element content (%): C, 89.28; H, 6.28; N, 4.50.

[0248] Synthesis Example 30: Synthesis of Compound 261

[0249]

[0250] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-261, B-261, and D-11 to obtain Compound 261 (18.51 g) with HPLC purity ≥99.98%. Mass spectrum m / z: 868.4402 (theoretical value: 868.4410). Theoretical element content (%) C 65 H 44 D7NO: C, 89.82; H, 6.72; N, 1.61. Measured element content (%): C, 89.79; H, 6.75; N, 1.59.

[0251] Synthesis Example 31: Synthesis of Compound 326

[0252]

[0253] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-326, B-326, and D-54 to obtain compound 326 (18.85 g) with HPLC purity ≥99.96%. Mass spectrum m / z: 884.4146 (theoretical value: 884.4130). Theoretical element content (%) C 67 H 52 N2: C, 90.91; H, 5.92; N, 3.16. Measured element content (%): C, 90.92; H, 5.95; N, 3.17.

[0254] Synthesis Example 32: Synthesis of Compound 350

[0255]

[0256] According to the preparation method of Synthesis Example 5, B-1 and D-1 were replaced with equal moles of B-350 and D-11 to obtain compound 350 (18.31 g) with HPLC purity ≥99.91%. Mass spectrum m / z: 835.3801 (theoretical value: 835.3814). Theoretical element content (%) C 63 H 49 NO: C, 90.50; H, 5.91; N, 1.68. Measured element content (%): C, 90.53; H, 5.88; N, 1.72.

[0257] Synthesis Example 33: Synthesis of Compound 362

[0258]

[0259] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-54, B-362, and D-11 to obtain compound 362 (18.68 g) with HPLC purity ≥99.94%. Mass spectrum m / z: 901.3726 (theoretical value: 901.3742). Theoretical element content (%) C 67 H 51 NS: C, 89.20; H, 5.70; N, 1.55. Measured element content (%): C, 89.17; H, 5.74; N, 1.59.

[0260] Synthesis Example 34: Synthesis of Compound 379

[0261]

[0262] According to the preparation method of Synthesis Example 5, B-1 was replaced with an equal molar amount of B-379 to obtain compound 379 (18.09 g) with HPLC purity ≥99.96%. Mass spectrum m / z: 825.3988 (theoretical value: 825.3971). Theoretical element content (%) C 62 H 51 NO: C, 90.14; H, 6.22; N, 1.70. Measured element content (%): C, 90.19; H, 6.20; N, 1.69.

[0263] Synthesis Example 35: Synthesis of Compound 413

[0264]

[0265] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-204, B-413, and D-11 to obtain compound 413 (19.06 g) with HPLC purity ≥99.95%. Mass spectrum m / z: 933.4381 (theoretical value: 933.4368). Theoretical element content (%) C 69 H 59 NS: C, 88.70; H, 6.37; N, 1.50. Measured element content (%): C, 88.68; H, 6.40; N, 1.53.

[0266] Synthesis Example 36: Synthesis of Compound 430

[0267]

[0268] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-430, B-430, and D-11 to obtain compound 430 (18.58 g) with HPLC purity ≥99.92%. Mass spectrum m / z: 937.4460 (theoretical value: 937.4475). Theoretical element content (%) C 71 H 51 D3N2: C, 90.89; H, 6.12; N, 2.99. Measured element content (%): C, 90.92; H, 6.08; N, 2.95.

[0269] Synthesis Example 37: Synthesis of Compound 433

[0270]

[0271] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-433, B-433, and D-11 to obtain compound 433 (18.85 g) with HPLC purity ≥99.96%. Mass spectrum m / z: 897.3837 (theoretical value: 897.3824). Theoretical element content (%) C 64 H 55 NSSi: C, 85.57; H, 6.17; N, 1.56. Measured element content (%): C, 85.61; H, 6.19; N, 1.53.

[0272] Synthesis Example 38: Synthesis of Compound 441

[0273]

[0274] According to the preparation method of Synthesis Example 5, A-1, B-1, and D-1 were replaced with equal moles of A-441, B-121, and D-11 to obtain compound 441 (18.42 g) with HPLC purity ≥99.93%. Mass spectrum m / z: 876.4091 (theoretical value: 876.4080). Theoretical element content (%) C 65 H 52 N2O: C, 89.01; H, 5.98; N, 3.19. Measured element content (%): C, 89.04; H, 5.93; N, 3.23.

[0275] [Device Example 1]

[0276] First, the glass substrate with ITO / Ag / ITO vapor deposited was washed three times in distilled water and ultrasonically washed for 20 minutes. After the distilled water washing, it was ultrasonically washed in sequence with isopropyl alcohol, acetone, and methanol solvents, and then dried on a hot plate heated to 120°C. The dried substrate was transferred to a plasma cleaning machine and transferred to a vapor deposition machine after washing for 5 minutes.

[0277] Then, HI-1 was vacuum evaporated on the cleaned ITO / Ag / ITO substrate as a hole injection layer with a thickness of 10 nm. HT-1 was vacuum evaporated on the hole injection layer as a first hole transport layer with a thickness of 60 nm. Compound 1 of the present invention was vacuum evaporated on the first hole transport layer as a second hole transport layer with a thickness of 40 nm. BH-1 was vacuum evaporated on the second hole transport layer as a host material, and BD-1 was vacuum evaporated as a doping material (mass ratio of 95: 5) to form a light-emitting layer with a thickness of 45 nm. ET-1 and Liq (mass ratio of 1: 1) were vacuum evaporated on the light-emitting layer as an electron transport layer with a thickness of 40 nm. On the electron transport layer, LiF was vacuum evaporated as an electron injection layer with a thickness of 1 nm. Then, Mg:Ag (mass ratio of 1:9) was vacuum evaporated on the electron injection layer to form a cathode with a thickness of 30 nm, and CP-1 was vacuum evaporated on the cathode to form a capping layer with a thickness of 60 nm, thereby preparing an organic electroluminescent device 1.

[0278]

[0279] [Device Examples 2 to 34]

[0280] Organic electroluminescent devices 2 to 34 were prepared by using the compounds 11, 17, 27, 37, 54, 61, 73, 87, 95, 106, 121, 127, 133, 147, 161, 176, 178, 191, 201, 204, 216, 231, 244, 261, 301, 326, 332, 362, 379, 413, 430, 433 and 441 of the present invention instead of compound 1 in device example 1 as the second hole transport layer. Except for this, the other preparation steps were the same as those in device example 1.

[0281] [Comparative Device Examples 1-2]

[0282] Comparative compounds 1 and 2 were used instead of compound 1 in device example 1 as the second hole transport layer. Other preparation steps were the same as those in device example 1 to prepare comparative devices 1 and 2.

[0283] A combined IVL testing system, comprised of testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectrum scanning luminance meter, was used to test the luminous efficiency and driving voltage of the devices prepared according to the present invention at atmospheric pressure and room temperature. The service life of the devices prepared according to the present invention was also tested using a McScience M6000 OLED lifetime testing system at atmospheric pressure and room temperature. The luminescence characteristics of devices 1-34 from the present invention's device examples and the organic electroluminescent devices obtained from Comparative Examples 1-2 are shown in Table 1 below.

[0284] [Table 1] Luminescence characteristics test of organic electroluminescent devices

[0285]

[0286]

[0287]

[0288] The results in Table 1 show that, compared with comparative devices 1 and 2, the use of the triarylamine compounds of the present invention as the second hole transport layer material in organic electroluminescent devices can effectively improve the luminous efficiency of the organic electroluminescent devices and extend the service life of the organic electroluminescent devices.

[0289] It should be noted that the present invention is particularly described using individual embodiments. For ordinary technicians in the technical field, several improvements and modifications can be made to the present invention without departing from the principles of the present invention. These improvements and modifications also fall within the protection of the present invention.

Claims

1. A triarylamine compound, characterized in that The triarylamine compound is represented by the structure shown in Formula 1: The A is selected from Formula 2: The R1 is selected from any one of the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl; the "substituted or unsubstituted" substituent in the R1 is selected from one or more of deuterium, tritium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl. When there are multiple substituents, the multiple substituents are the same or different from each other; The R2 is independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted any one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; The a is independently selected from 0, 1, 2, 3 or 4; when the a is greater than 1, two or more R2 are the same or different from each other, or two adjacent R2 are connected to form a substituted or unsubstituted benzene ring; The L is selected from a single bond or any one of the following groups: The R7 is independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted any one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; The e1 is independently selected from 0, 1, 2, 3 or 4; the e2 is independently selected from 0, 1, 2 or 3; when the e1 or e2 is greater than 1, two or more R7 are the same or different; The Ar1 is selected from any one of the following groups: The R3 is independently selected from hydrogen, deuterium, tritium, any one of the following groups which are substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, and adamantyl; and one or two of the R3 are selected from substituted or unsubstituted adamantyl; the substituents of the "substituted or unsubstituted adamantyl" are independently selected from deuterium, tritium, and any one of the following groups which are substituted or unsubstituted by deuterium: methyl; The R a 、R b independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted any one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, biphenyl, naphthyl; The R c independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted any one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; b1 is independently selected from 1, 2, 3, 4, or 5; b2 is independently selected from 1, 2, 3, or 4; b3 is independently selected from 1, 2, 3, 4, 5, 6, or 7; b4 is independently selected from 1, 2, 3, 4, 5, or 6; b5 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; b6 is independently selected from 1, 2, 3, 4, 5, 6, 7, or 8; b7 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; b8 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12; b9 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14; when b1, b2, b3, b4, or b5 is greater than 1, two or more R3 are the same or different from each other; The Ar2 is selected from any one of the following groups: R4 is independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted any one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, trimethylsilyl, triethylsilyl, tri-tert-butylsilyl, triphenylsilyl; The R5 is independently selected from any one of the following substituted or unsubstituted groups: phenyl, biphenyl, naphthyl; Said c1 is independently selected from 0, 1, 2, 3 or 4; said c2 is independently selected from 0, 1, 2, 3, 4, 5 or 6; when said c1 or c2 is greater than 1, two or more R4 are the same or different from each other; The L1 and L2 are independently selected from a single bond or any one of the following groups: The R9 is independently selected from hydrogen, deuterium, tritium, substituted or unsubstituted any one of the following groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; The f1 is independently selected from 0, 1, 2, 3 or 4; the f2 is independently selected from 0, 1, 2 or 3; when the f1 or f2 is greater than 1, two or more R9 are the same or different from each other; Except for R1 and the "substituted or unsubstituted adamantyl group", the remaining "substituted or unsubstituted" substituents are selected from one or more of deuterium and tritium.

2. The triarylamine compound according to claim 1, characterized in that The R2 is independently selected from hydrogen, deuterium, tritium, or any one of the following substituted or unsubstituted groups: methyl, isopropyl, or tert-butyl.

3. The triarylamine compound according to claim 1, characterized in that The Ar1 is selected from any one of the following groups: The R3 is independently selected from hydrogen, deuterium, tritium, any one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, adamantyl; and one of the R3 is selected from substituted or unsubstituted adamantyl; The R a 、R b Any one of the following groups, which are substituted or unsubstituted, is independently selected: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl; The R c Independently selected from hydrogen, deuterium, and tritium.

4. The triarylamine compound according to claim 1, characterized in that The Ar2 is selected from any one of the following groups: The R4 is independently selected from hydrogen, deuterium, and tritium.

5. The triarylamine compound according to claim 1, characterized in that The L is selected from a single bond or any one of the following groups: The R7 is independently selected from hydrogen, deuterium, and tritium.

6. The triarylamine compound according to claim 1, characterized in that The L1 and L2 are independently selected from a single bond or any one of the following groups: The R9 is independently selected from hydrogen, deuterium, tritium, and any one of the following substituted or unsubstituted groups: methyl.

7. A triarylamine compound, characterized in that: The triarylamine compound is selected from any one of the following structures:

8. An organic electroluminescent device comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode, characterized in that: The organic layer comprises a hole transport region, and the hole transport region contains any one or a combination of at least two of the triarylamine compounds according to any one of claims 1 to 7.

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